Entourage Troubleshooting

Revision as of 09:57, 19 November 2009 by Christopher Hunt (talk | contribs) (Entourage moved to Entourage Troubleshooting: This is a Helpdesk-facing page. Linda will appropriate the public documentation page.)

Entourage is the only officially supported e-mail client on the Mac.

General Entourage Issues

Certificate Errors

Problem: Entourage warns you that the certificate for autodiscover.middlebury.edu is not trusted.

  1. Install the Middlebury College Certificate according to these instructions: https://mediawiki.middlebury.edu/wiki/LIS/Certificate_Errors#Mac_OS_X
  1. Open Entourage (and enter your password if prompted). Try composing a dummy e-mail message.
  2. If the certificate error doesn't appear, you're all set and do not need to follow the instructions below.
  3. If the certificate error appears again, you need to update Entourage's LDAP server (instructions below):
    1. Click on the Entourage menu (top left corner, next to apple logo) and select "Account Settings".
    2. Double-click the exchange account, you will recognize the exchange account because it ends with the word (exchange).
    3. Click the "Advanced" tab. Near the middle of the window, under Directory Settings, ensure that the LDAP server is puma.middlebury.edu
    4. You can leave the other settings as they are. Click the OK, button and enter your e-mail password if prompted.
    5. Try composing a dummy e-mail message. The certificate error message should not appear.

Entourage 2004



Known Issues

Changing the subject of a message

  • It's not possible to change the subject of a message (this is possible in Outlook). There is an add-on that can help Entourage do this:


Slow Entourage and Spinning Beachball

When I type an email recipient's name in Entourage the "check name" feature doesn't work


In Entourage when you type a recipient's name ("Last Name, First Name") in the "To:" or "CC:" field of an email message it doesn't recognize the name and the "Check Name" button doesn't work.


The LDAP settings for Entourage are probably not correct.


1. In Entourage, go to: Tools/Accounts, then Edit to access the account. 2. Clicked Advanced. 3. Make sure the LDAP is set to ad.middlebury.edu. You also needed to UNcheck the box beside "server requires log on."

Applies to

Entourage X and 2004 with an exchange account (NOT POP, NOT IMAP)

Tracking details: Author: P.M. Revised: 11/04/2007

How do I delete attachments from email messages in Entourage?

In Entourage, the "Remove" attachment button is available for POP and IMAP accounts, but not for Exchange accounts (most Middlebury accounts are set up as Exchange accounts). Thus, you cannot remove a single attachment from a message, instead you can only remove ALL attachments from a specific message. To do so: 1. Double-click the message to open it in a new window. 2. From the Message menu in Entourage select "Remove All Attachments". This will remove all attachments from the opened message.

Microsoft is aware of this behavior but has not indicated when will it be improved.

Applies to

Microsoft Entourage X and 2004

Tracking details: Author: P.M. Revised: 11/04/2007

Finding Large Email Messages in Entourage

  • Right-click (or hold Control when clicking) on the top-level folder of your email account in the folder list on the right-hand side of Entourage.
  • Choose Folder Properties.
  • Click on the Storage tab.
  • Youll see a list of your folders and how much space they use. You can click the heading buttons to sort in different ways (such as by size).

You can easily add a column displaying the size in any folder view. To do this, just right-click (or hold down the control key and click) on the header bar above the messages, then choose Size from the drop-down list. You can then sort by size by clicking on that heading button.


You can create a Mail View to locate the large emails. (Mail views are the Entourage equivalent of the "Search Folders). To create a mail view,

  • right-click on the Mail View folder, then choose New Custom View.
  • Give your view a name (such as Big Mail), check the box to show messages and then set up the criteria area.
  • You can use the pull-down lists to create an instruction to look for size greater than 100 K.
  • Click OK when youre finished setting up the view. The new view will now appear in the Mail View list just click on the folder and youll see all the messages that meet your criteria.

Entourage 2004 is moving messages from folders on the exchange server to "Folders on My Computer"


Some users running Entourage 11.2.1 as an Exchange client have had messages removed from folders on the Exchange server (Inbox, Sent Items, etc.) and moved into the Inbox under "Folders on My Computer"


The exact cause is not apparent, but most of the users experiencing this problem have set up Entourage as an IMAP client and switched back to an Exchange client. This behavior also started close to the December 28th, 2005 upgrade of the mail server.


Create a new Entourage identity.

Before creating a new profile, be sure to backup any of the "Folders on My Computer" by dragging them to the Desktop. Once a new identity is created any items located in "Folders on My Computer" will be lost.

  • In Entourage, select Switch Identity from the Entourage menu
  • In the dialogue box that pops up, New
  • Enter a name for the new Identity and click OK
  • You will be prompted to set-up Entourage from scratch.

Tracking details: Author: P.M. Revised: 1/28/2008

Changing font size in Entourage

When you have a message open in Entourage you can decrease the font by:

  • choosing Edit/Decrease Font Size


  • pressing Shift+CMD+Minus sign (repeat as needed)

Viewing Shared Calendars

It is really handy for departments to share calendars. They are of little use if you cannot view them though. We have a guide on how to do it here Add another mailbox to Entourage. The Illinois State University also describes how you can do it in Entourage.

Entourage 2008



Known Issues

See Known Issues and Entourage vs Outlook

Changing the password in Entorurage

Middlebury College requires that you change your password every 6 months. When you change your password, Entourage does not automatically receive the new password. Instead you need to manually change it inside Entourage.

  1. Open Entourage
  2. Click on the menu titled "Entourage" (top left corner, next to the apple logo)
  3. Click Account Settings
  4. Double-click the account whose password you'd like to change
  5. On the first screen, under "Receiving Mail" there will be a space for the password.
  6. Erase whatever password is there.
  7. Type the new password in. In addition, if this is a POP or IMAP account:
    1. Click on "Click here for advanced sending options"
    2. Ensure that the option "SMTP server requires authentication" is selected,
    3. Set it to "Use same settings as receiving mail server"
  8. Click OK


  • Repeat the above procedure for any other affected accounts (including any "Directory Service" accounts, these can be access using steps 1-3 above, then click on the "Directory Service" tab)
  • To avoid having to update the password in Entourage in the future, you can tell Entourage to always ask you for a password. To do so, follow steps 1-7 then click "OK".
Powered by MediaWiki